Pleasant Valley Vacation Packages

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Your Pleasant Valley Vacation

The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or choose someplace else — our packages are all about you. If your trip to Pleasant Valley includes some sightseeing, visit renowned attractions like Marist College, Vassar College and Culinary Institute of America. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Pleasant Valley vacation is easy with Expedia.

Top Pleasant Valley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
5.4/10 (1,004 reviews)
The person on staff was kind, friendly , helpful that was the night staff The morning staff was also friendly and nice

Reviewed on Aug. 12, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
5.8/10 (1,002 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul. 8, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
7.4/10 Good! (502 reviews)
Comfortable place to stay

Reviewed on Aug. 7, 2025

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.4/10 Very Good! (1,001 reviews)
The property is nice, near to Legoland, grocery, and fast foods.

Reviewed on Aug. 14, 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.2/10 Wonderful! (926 reviews)
Everything was great

Reviewed on Aug. 13, 2025

Ready to book your vacation to Pleasant Valley?

 

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Pleasant Valley Hotel Deals

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Aug 24 to Aug 25
CA $181
CA $203 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Other than the arcade being a joke and taking our money while literally 2 games worked, we had a nice stay. Chose the hotel for pool and arcade, so slightly disappointed. Pool was nice, clean and warm. We had it to ourselves which was nice. Front desk staff was extremely friendly and helpful."

Reviewed on Aug. 8, 2025

Best Western Plus Kingston Hotel And Conference Center
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is CA $1,378 per night from Sep 1 to Sep 2
CA $1,378
CA $1,603 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (51 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

Wildflower Farms, Auberge Resorts Collection
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is CA $129 per night from Sep 15 to Sep 16
CA $129
CA $153 total
Sep 15 - Sep 16
includes taxes & fees
7.2/10 Good! (512 reviews)
"Comfortable place to stay"

Reviewed on Aug. 7, 2025

The Crossroads Hotel, Newburgh
See all 1,114 properties in Pleasant Valley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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What to do in Pleasant Valley

Have you hugged an alpaca today?

Alpaca and Llama Trek in Pleasant Valley

CA $66
per adult
Alpaca and Llama Trek in Pleasant Valley
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

CA $92
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Pleasant Valley

Frequently asked questions

How much does a Pleasant Valley vacation package cost?
You'll find cheap prices from CA $636 on Expedia for your Pleasant Valley escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Pleasant Valley costs.
What are the cheapest months to go to Pleasant Valley?
To pick up cheap Pleasant Valley vacation packages, plan your getaway outside of peak periods such as public holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Pleasant Valley?
We'd suggest booking a Pleasant Valley vacation for at least 3 days. This gives you enough time to check off popular sights including James Baird State Park and Vassar Golf Course, and check out neighbourhoods like Arlington and Fairview. You might even be able to slot in a day trip or two from Pleasant Valley.
How to find the best Pleasant Valley package deals?
Landing a cheap Pleasant Valley package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Pleasant Valley package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Pleasant Valley vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Pleasant Valley vacation by choosing your favourite type of stay, airline and car class.
How to plan a trip to Pleasant Valley?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Pleasant Valley.
  2. Set your budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Pleasant Valley. Then, choose a hotel that works with your budget, whether that's a low-cost option or a swankier retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Pleasant Valley. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, lock in the right Pleasant Valley vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.